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Paper | Regular issue | Vol 48, No. 2, 1998, pp.285-294
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8053
■ The Dakin-West Reaction of N-Acyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acids Using Trifluoroacetic Anhydride: Structural Revision for the Unexpected Product

Masami Kawase,* Youichi Okada, and Hiroshi Miyamae

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japana

Abstract

The Dakin-West reaction of N-pivaloyl- and N-benzoyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acids (1a-e) with trifluoroacetic anhydride yielded unexpectedly 1-(1-acyloxy-2,2,2-trifluoroethyl)-3,4-dihydroisoquinoline derivatives (3a-e) in good yields. Among of the products (3), the structure of 3b has been confirmed by X-Ray crystallography. The carbamate derivatives (1h, i) gave 1-trifluoroacetyl-N-acyl-1,2,3,4-tetrahydroisoquinolines (4e, f), the Dakin-West reaction products, as a main product. The reaction of N-acetyl derivative (1g) produced completely different type of the product (5).